


The First Orgasm

by LavenderNomad



Series: A First Time For Everything [1]
Category: Supernatural
Genre: Cum Play, Cum shot, Do not duplicate, F/M, First Time, Masturbation, Multi, No Incest, Porn, Reader Insert, Second person POV, Tenuous plot, Threesome, Vaginal Sex, Virgin Reader, cis female reader, imagine, unprotected sex, use a condom irl ok kids!!!
Language: English
Status: Completed
Published: 2016-07-25
Updated: 2016-07-25
Packaged: 2018-07-26 15:44:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,728
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7580116
Author URL: https://archiveofourown.org/users/LavenderNomad/pseuds/LavenderNomad
Summary: <blockquote class="userstuff">
              <p>Look, it's not that weird to be in your twenties and a virgin, alright? Now if only these damn Winchesters would leave you alone about it... But, you know. Not really.</p><p> </p><p>Prompt: "Imagine Dean watching as Sam takes your virginity and gives you your first orgasm."</p>
            </blockquote>





	The First Orgasm

**Author's Note:**

> I would say this takes place earlier in the series, so they’re still in their early/mid 20s.
> 
> Unprotected sex but let's say that the reader has an IUD or perhaps is infertile or something. If you don't have these, please use condoms IRL.

“What do you mean you’ve never done it?”

“Shh!” You exclaim, struggling to shove your hands over Dean Winchester’s mouth, a blush forming violently across your cheeks. “Don’t say it so loud! Geez…” 

The smoky bar isn’t packed but it isn’t empty; one of those cliché dive bars. It has wooden floors and bartops, wooden shelves of dusty liquor and just a few taps for beer; a pool table and darts board completed the scene. The alcove you and the boys were sitting in was hidden just out of view of the main bar, but it wasn’t private per se. The murmur of voices barely drowned out some background guitars and twangy voices. 

You feel his stupid smirk underneath your hands before his body shakes with laughter, trying to push your hands back. “Sorry it’s just… Come on! Aren’t you like 20? Shouldn’t it have happened by now?”

“Leave her alone, Dean,” Sam scolds, but when you turn to face him, there is a curious light in his eyes; he regards you differently, more predatorily. “Is there a reason for it … never happening?”

You gape; you had been hoping that had been the end of the conversation, not the beginning of a path you didn’t want to go down. You grimace, taking a sip of your beer; you had to be more than just buzzed for this. “I dunno, just never got around to it, I guess. Not a self-esteem thing but… I just couldn’t wrap my mind around the idea of people wanting to sleep with me, I still feel like a naïve kid for fuck’s sake.” You look up at them; both the Winchester boys are laser focused on you, their poker faces on but their eyes speaking volumes about what you belatedly realized was desire. “Wait, what? Don’t tell me you guys are turned on by that.” They were silent, but Sam looked uncomfortable, suddenly avoiding your eyes and Dean smiled wide. “Why—what the fuck? You guys are turned on by virgins? How do you know I wouldn’t just—I don’t know---twist myself wrong and break your goddamn penis! I have literally no experience!” You grow more and more flustered, heat spreading all over your body—partially from embarrassment, partially from how their gazes travelling over you feels. 

Dean smirks. “As a penis-owner, I can attest that the penis can take a lot of movement.”

“Dean!” you give him an affronted look, attempting to swat at his beer. Sam snorts. “Sam! I thought you were better than just wanting a girl for whatever weird… physical… something or one thing—“ you sputtered. 

He chuckles at your extreme embarrassment, brushing some hair behind your ear. “That’s not the only thing I like about you, moron.” His hand lingers by your ear, and you feel yourself tingling. 

_‘Is that…? A confession?’_

You were bewildered. 

“Yeah, you’re hotheaded as hell, but you’re smart; you hold your own when we’re hunting, and you’re pretty damn nice too,” Dean adds. His voice is joking, still, but his eyes are soft, emanating affection. “Who couldn’t fall in love with someone like that?”

_‘What the fuck is happening right now?’_

You clear your throat, panicking. Their gazes are heavy and meaningful on you and the air is heavy suddenly. You quickly take a sip of your beer, avoiding their eyes. It was too much to process at once; you had pushed your feelings for them away for so long, for the sake of safe hunts and no awkward relationships that you were a hurricane of confusion, of attraction, of happiness. You almost jump when your phone goes off, indicating an e-mail. Hurriedly, you look at it; anything to get out from under their gaze.  
BUY ONE GET ONE FREE! All swimsuits now….

You delete it; there’s no shopping on a hunter’s paycheck. When you look up, the moment is broken, and Sam and Dean are arguing if the hauntings by Disney at Disneyland were serious enough to warrant a case. Relieved but somehow disappointed, you pick your beer back up and join in the bantering.

\--  
They always rented two bed motel rooms, and everyone always cycled in sleeping arrangements; Sam and you, then Dean and you, then Sam and Dean. You usually undressed in the same room as the boys, just facing another corner, assuming they didn’t see you that way. Maybe it was denial, but if you believed that, it made the idea of indefinitely travelling with them more bearable; after all, there wouldn’t be weird awkward relationship stuff interfering with hunting, right? _‘So I missed all those signs,’_ you berated yourself. 

But tonight, especially after the conversation at the bar, you feel somewhat shy. Both the boys are wildly attractive; Sam, with his rugged good looks and irresistible long hair and sweet attitude and Dean, with his bad boy charm, huge beautiful eyes and confidence. There was something so good about both of them, but so pained in them. You wanted to protect them at all costs, to make sure they could be as happy as possible in their lives. 

You awkwardly pick up your pajamas, suddenly aware of just how tight and short they are. Trying your best to act normal, you jump into the shower, cleaning yourself of the smoke and beer from the bar. 

A part of you was giddy; both of them had expressed interest in you and this kind of attention from people you liked and knew was rare. It wasn’t the awkward grocer hitting on you or the sleazy weirdo at a bar; it was Sam and Dean Winchester. It was the boys, your boys. 

Toweling your hair off, trying to make how it fell over the front of your body look natural and not like you are hiding, you exit the door, the room very cool compared to the bathroom. Sam is reading a newspaper in bed, Dean nowhere in sight. You were supposed to be sharing a bed with Sam tonight, but you cross to the other bed and sit on it, facing the TV. Flipping it on, you cross one leg under you as you flip through the channels.

“Where’s Dean?” You ask absently, rubbing your hair between the towel. Giving up, you drape it over your shoulders, letting water run down your back. You hear paper shuffling, and bed springs. 

“Checking on Baby, he said. He should be back soon. You want this bed tonight instead?” Sam sits down next to you, the bed bouncing gently. You turn your head, and you blush immediately at the focus and gaze he has on you. 

“Oh… um…” You nod, turning back to the tv, flipping the towel over your head as you crawl to one side of the bed. You pull the pillow out and fluff it, trying to avoid looking at Sam. He scoots up the bed, leaning against the head board and you turn around and do the same. Though the bed is a queen, Sam leaves barely a few inches of space between your hips and the shaggy-haired man. You pull your knees up, and Sam pulls you against him, arm around your shoulder. You stiffen before relaxing—this was normal, just some contact at the end of long days. You pull the towel off and throw it on the ground. His scent washes over you and you lean further in. The tv forgotten, he tilts your chin up a little. His breath is so close, fanning over you. He presses his nose gently against yours and your nerves light on fire. You are so aware of this moment, his flannel against your bare arm, the scratchiness of the motel blankets against your thighs, the closeness of his face. 

You didn’t know what you were doing, but you didn’t want to stop.

It feels like forever, his nose pressing and rubbing gently against yours. You don’t know when your eyes closed, you know nothing but his hand on your arm rubbing gentle shapes, his scent, his skin. 

You aren’t sure who moves, but your lips are suddenly pressed together. Your hearts brims with emotion, you crane your neck to reach him, to press your lips harder against his rough, dry ones. He turns his chest, both hands moving to cradle your face. You turn, too, to press against his shoulders, your abdomen awkwardly splayed across Sam’s. Fireworks explode under your skin, and you feel his lips part to tentatively yet brazenly draw itself against yours. You hesitate, opening just wide enough for him to slip his tongue against your lips. You moan. How can this feel so good? How can you feel so good, so safe?

Strong hands pull you and lift you into his lap, your thin pajama shorts rubbing against his jeans. His hands still at your hips. You relax your thighs so you are sitting on him, and he groans feeling your weight against him. Now you are tilting your head down, gently biting his lower lip and he opens his mouth, pressing and working his jaw against yours. Your core warms up, and you move your hands from his chest to his neck, gently holding his neck. It is strong, warm, comforting. He breaks away to gaze against you. Your eyes are hooded as you look back, biting your lower lip. His eyes are drawn to the motion, his own lips swollen. Sam’s eyes are soft and gentle, drinking in your face. His brow is crinkled just slightly, like he is thinking over something.  


“You know both Dean and I... we really care about you.” He stumbles through his words, his voice a low husky whisper. You smile, press a kiss to his nose. 

“I know. I really care about you both too.” 

This answer seems to satisfy him. His lips move up to capture yours again, desperate and hungry. It’s different, and he seems to be holding something back instead. You pull away, kissing gently along his jaw, his eyes clenched as tight as his hands are around your hips. Tentatively, you pull his lobe between your teeth and he groans. You become aware of his hardness pressing directly against your core, and you begin suckling on his ear lobe. Letting go, you leave a wet lick behind his ear and kiss down his neck, sucking and kissing. He groans, fingers inching under your shorts, pressing the skin of your thighs, gently moving your hips along him. He seems to be at a breaking point, trying so hard to be delicate with you.

His eyes fly open as you lick his pulse and he leans pushes you forward, so your head is now at the foot of the bed, and he soon follows. Sam kisses you breathless, before sucking his way down to your collarbone. The tank top strap of your pajamas slips down and he growls, rubbing the skin there. You moan wantonly beneath him, your legs spread so he fits against you. The shaggy haired man leans back to survey you, growling in approval at what he says as you gasp breathlessly. 

At that moment, the door swings open and you almost knock into Sam’s jaw as you shoot up. He keeps you pinned and so you lay back and you are forced to sheepishly look at the older Winchester brother upside down. His smirk is recognizable. “So little brother, got to work on baby’s first orgasm, huh?” There is laughter but invitation in that voice. Affection and promises of a long night. 

There is no denying that; and you blush. 

“Shut the door, asshat,” Sam says. Dean complies, fluidly sliding his jacket off and stepping to you and kneeling down, smiling. His eyes appreciatively travel along your body, the smile growing just that much wider. He kisses you upside down, his kiss rougher, more lusty, his tongue brushing harshly against you. Sam returns to kissing and sucking at the juncture of your neck and shoulder, one hand sliding up your side. One of Dean’s hands bypasses all ceremony and he palms your breasts over your top, rubbing the nipples hard, tweaking just hard enough for you to gasp into his mouth. 

Suddenly he moves away, pulling a chair up. There is a bulge in his jeans already and he rubs a hand over it, his eyes smoldering. Realizing he intends to watch, you grow hotter, pulling Sam down by the collar of his shirt to kiss him. You sit up, Sam leaning back, breaking the kiss to pull his shirt off. Desperation is evident in his movements now, and you run a hand over the ripping muscles, pressing a kiss to the chest of the kneeling man, a tongue instinctively licking around his pectorals. You feel yourself grow hotter at the salty taste of his skin, your hands snaking over his back. 

“No,” he pants, gently pressing you down again. “Not right now.” He kisses you, tugging at the hem of your shirt, and you arch your back so he can remove the top. You hear Dean’s groan of approval, hear the zipper of his pants. You tilt your head to see the older Winchester’s cock rock hard, his own hand lazily sliding up and down the length, his eyes focused on you. You look back at Sam, crossing your arms under your breasts, pressing them up and together. Sam presses his hand against your breast, licking all around your nipple. His palming, strong but slow, tightens a coil in you. You writhe, wanting him so desperately to touch you where you needed him, rubbing your crotch up at him.

He finally wraps his lips around your breasts, circling it with his tongue and sucking, his palm still gripping the other breast. His other hand slides beneath your back, down so he is squeezing your ass. You moan, whining and keening for more. You squint at Dean, who is more intently rubbing his dick, his jaw tight, eyes dark as they catch your gaze. You lick your lips and he moans, thrusting particularly hard into his own palm. Sam presses your breasts together, somehow managing to wrap his mouth around both nipples at once. He gives an experimental suck, hands gripping your breasts together tightly, and pleasure surges through you.

“Sam… please… more please…” You can almost feel the effect of your words on both brothers, the air suddenly electrifying. Sam hooks his index fingers into the sides of your pajama shorts, grabbing your ankles up to slide them off so he can remain with himself against you. He throws it at Dean, who grunts. 

“See how wet she is, Dean?” You look upside down at Dean, who opens up your shorts. Your sticky wetness is apparent.

“Oh fuck,” Dean says appreciatively, wrapping it around his length, his eyes closing as he rubs his dick experimentally. 

Your attention returns to same when he lets your legs drop around him and he presses himself—still clothed—against your heat. “Fuck, if I had known you slept without panties…. It’s been hard enough with you sleeping next to me with no bra. You would’ve made things painful.”

“You naughty girl,” Dean agrees, slowly rubbing himself still. “Do you sleep like that every night?”

You nod. “I trust you both.”

Sam hovers over you, forcing your gaze on him. His eyes flit back and forth between each of yours. 

“Sam… I want it,” you say, softly, confidently, afraid. He smiles, finding out what he wanted, and he kisses you while you feel his hands undo his jeans. You pat at his chest, wanting to see him. He moves back, letting you watch as he pulls his pants down his waist, and pulls his cock out. You moan upon seeing it, the head red and swelling, precum coating it. You are so hot now, and you whine, brushing your folds up along his length. Sam’s eyes close, his jaw ticking. You hear Dean move the chair forward, and you try to move your hips along Sam again, wanting both men to groan for you. Sam’s hands press against your hips, and you pout up at him. He kisses you again, before pushing your legs out further, and rubbing his cock once more against your wetness. His dick comes away wet and he moans. 

“You’re fucking soaking. You ready for me, baby?” You wriggle your hips in assent, wanting his cock against your clit. Your head falls back to watch Dean pumping a little harder on his cock, watching the scene intently.

Sam gently takes hold of his cock, pressing the head against you. He moves it in shapes along your folds, and you moan, wanting more. Gently, he presses the head into you and you gasp, eyes fluttering. He pushes into you, and you feel yourself stretching around him. There is no pain, just a slight discomfort and he pumps experimentally. When you wince, he stops. 

Soon, your nerves leave and you feel so full of him, you can hardly believe this is happening. His cock in your pussy feels so good and you jut your lips up against him, pleasure shooting up your spine. He groans, eyes telling you to wait. 

You don’t want to. You thrust into him again, moaning loudly. Breaking, Sam begins pushing himself in and out of you. The feeling is exquisite and you throw your head back moaning loudly, only to groan at the sight of Dean’s hand wrapped around his own cock, biting his lower lip. 

Sam lifts your hips just slightly, so your lower back is resting against his kneeling knees and he renews his thrusting. You see his eyes roll into the back of his head, his lips mouthing “oh fuck” and your name over and over again. The new position makes him feel bigger inside you, and you wriggle your hips on his cock. 

Soon Sam is pounding his member into you, the sound of skin slapping and wet pushes filling the room along with all three of your moans. The younger Winchester slows to hunch over you and kiss you before leaning back, holding your hips as he slams his cock against you. You clench your inner muscles over him, and he groans in response, rewarding you with an extra, unbridled thrust.

“Oh god, please more,” you aren’t even aware of yourself saying, your skin on fire. You feel Dean’s hand on your cheek, the sound of him fucking his palm closer to your head. You look up to see him hunched over you, intently watching you. You whine at the sight of his hardness near you, eyes watching the head produces wetness which Dean uses as lubricant. Your pajama shorts are soaked around his cock. 

Sam’s thrusts become wilder and wilder, hitting every part of you. The coil in your belly grows tighter and tighter, and you helplessly try to thrust back at him, wanting so desperately to reach completion. Sam throws one of your legs over his shoulder, gripping your other leg to pull you impossibly closer, his cock now just pumping wildly in you. 

“Do you like the feeling of my cock in you? Do you like me fucking you, baby?” His voice is a dangerous growl and you nod, unable to answer with words. 

He is sliding in and out of you so fast now, your pussy and his cock providing so much lubrication. The friction against your clit, the feeling of his balls against you drives you wild. You feel Sam drop a hand down, circling your clit with his calloused thumb, and you moan. You look up at him, his face focused on yours, intense and dark and passionate. Your eyes slam shut, your muscles spasming as you feel the brink of an intense wave of pleasure.

“I-I… I think I’m gonna—“

The Winchester in your pussy angles his thrusting upwards ever so gently. “Cum, baby, fuck.”

His sentiments are mirrored by his brother, “Oh fuck, baby girl, cum for us.”

Their deep voices reverberate, and you cum, hard, clenching tight around Sam. Your chest tightens and you gasp. 

Sam’s movements have lessened, impeded by your walls intensely clenching around him, but he picks up, riding your very first orgasm out, stars sparkling behind your eyelids.

“Fuck, I’m gonna cum, I’m gonna cum baby,” Sam tells you, teeth clenched.

Your chest heaving, “Cum, Sam, cum.” He presses himself as tight as he can against you and you feel his cock twitching. Something warm slips down your thigh as Sam thrusts softly into you, filling you with his seed. 

Dean presses a hand against your cheek getting your attention. “I’m gonna cum all over you baby, ok?” you nod, wanting to feel Dean’s essence, wanting to be close to him. He stands over your face, pumping his cock alarmingly fast, your shorts a wrinkled mess around his cock and with a groan, his thighs and his jaw clench and white semen spills onto your face and chest. You moan feeling the sticky warmth all over you.

Sam finally pulls out while Dean is gently rubbing his cock, telling you how amazing you look painted with his cum. You are spent; it had been a long day on top of your first time. Sam is at the head of the bed, pulling the sheets back. Dean throws the towel you had earlier onto you, gently rubbing your face as he picks you up. You are limp and he chortles. “Baby girl, you ok there?” 

“’m tired now,” You murmur, curling up against his chest. He drops you unceremoniously next to Sam who lays you flat, gently kissing your wet forehead. You gaze sleepily at him. “Guess I sexed you up pretty good, huh?”

You grumble at being awake, and turn your back on him, as Dean lifts the sheets from the other side, the other bed completely forgotten for tonight. You feel Sam shift to lay behind you, curling himself against you, an arm wrapping around you waist and he kisses your shoulder. Dean presses his face to yours, kissing you, and you whine, wanting him but so, so tired. You open your eyes blearily to his face, a gentle smile you rarely saw on it. “Don’t worry, girl, I got you tomorrow night.” You smile at the promise and drift off to sleep, surrounded by the Winchester boys.

**Author's Note:**

> Seriously use condoms if you don't know them, or use any other form of birth control, ya hear me?


End file.
